Volume 26, Issue 9
Heterocyclic Compounds
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ChemInform Abstract: Cycloadditions of Methano(11)annulenones with Dichloro- and Chloro- Ketenes. Preparation of 2H-Methanocycloundeca(b)furan-2-one Ring Systems.

M. NITTA

M. NITTA

Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan

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H. TOMIOKA

H. TOMIOKA

Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan

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A. AKAOGI

A. AKAOGI

Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan

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K. TAKAHASHI

K. TAKAHASHI

Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan

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K. SAITO

K. SAITO

Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan

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K. ITO

K. ITO

Dep. Chem., Sch. Sci. Eng., Waseda Univ., Shinjuku, Tokyo 169, Japan

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First published: February 28, 1995

Abstract

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ChemInform Abstract

Cycloaddition of the title compounds (I) and (V) with dichloroketene yields the chlorinated cycloundecafuranones (III), (IV) and (VI), resp. , which are transformed into the unchlorinated parent compounds by reductive elimination with an excess of NaI in TFA. In contrast, cycloaddition of (I) or (V) with chloroketene yields chloroacetyl derivatives (IX)-(XI) and the parent compound (VIII).

chemical structure image

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